DNA intercalating properties of tetrahydro-9-aminoacridines. Synthesis and 23Na NMR spin-lattice relaxation time measurements.
A series of 9-(arylamino)-1,2,3,4-tetrahydroacridines, including the tetrahydro m-AMSA [N-[4-(acridin-9-yl-amino)-3- methoxyphenyl]methanesulfonamide] derivative, has been synthesized. 23Na NMR spin-lattice relaxation rate (1/T1) measurements have been used to study whether these hydrogenated acridines were capable of intercalative binding to calf thymus DNA. The results have been compared to corresponding measurements for 9-aminoacridine, m-AMSA, and MgCl2. All compounds studied were capable of intercalative binding to DNA. However, it was found that the interaction was strongly influenced by substituents on the 9-arylamino group. Thus, tetrahydro m-AMSA was found to intercalate much more weakly with DNA than m-AMSA. Removal of the 3'-methoxy substituent of the 9-arylamino group resulted in intercalation in DNA that was almost as strong as that for m-AMSA.
Dinesen
J
J
Department of Chemistry, Odense University, Denmark.
Jacobsen
J P
JP
Hansen
F P
FP
Pedersen
E B
EB
Eggert
H
H
D000585:Aminacrine / Q000378:metabolism; D000609:Aminoacridines / Q000138:chemical synthesis / Q000378:metabolism*; D000677:Amsacrine / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism*; D007364:Intercalating Agents; D015636:Magnesium Chloride / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D013329:Structure-Activity Relationship
D000609:Aminoacridines; D007364:Intercalating Agents; D000677:Amsacrine; D015636:Magnesium Chloride; D000585:Aminacrine; D004247:DNA